MILTON — When he was 13 years old Ian Manuel shot a woman in the face in a botched robbery in Tampa. She lived and he got life. • Manuel, now 33, has spent nearly all of his time in prison in solitary confinement, caught in an endless cycle of misbehavior and punishment. As Florida's longest-serving inmate in solitary, he has no work skills, no formal education and so much psychological damage that he once set himself on fire. • People always assumed — whether he killed himself or died of old age — that Ian Manuel's death would happen behind bars. Not anymore. • He may walk out of prison in the next year. • The U.S. Supreme Court is considering two Florida cases that deal with the constitutionality of locking away children for life when they haven't killed someone. A favorable ruling in either case could result in Manuel's sentence being thrown out. • Confronted with the possibility of his release, prison officials, who had kept Manuel as far away from civilization as they could, are scrambling to prepare him for life outside. And his attorneys are laying out a plan that will attempt to protect Manuel from a world he fears will present him with more choices than he can handle. • "The uncertainty out there makes me nervous," he says, "but I'm determined to succeed."

When he began his sentence in a tough adult prison at age 14, he was small and defensive. Afraid to appear vulnerable, he got into trouble immediately. He'd veer into the grass instead of walking on the path in the prison yard. When guards yelled at him, he'd yell back. When they came at him, he'd make obscene gestures. In less than a year, he was in solitary.

From there, the disciplinary infractions multiplied — for storing aspirin, for sticking his hand through the food flap, for standing at his cell door, for masturbating and for cursing. He would go six months at a time lying on his bed in what he called "a state of hibernation" to stay out of trouble. But it didn't matter. Each infraction added months and after a while the hole was so deep he couldn't get out.

Recently, he received a visit from someone not on his legal team. It was his first in 15 years. Leaning forward toward the glass separating him from his visitor, he tried to explain what kept him there:

"I'd tell myself to keep quiet and behave. But I was so desperate I couldn't control my impulses."

The result has been a life stripped of life.

No programs or education. No visitors, phone calls or human touch. No books, magazines, TV or radio. No talking. No standing at the cell door and looking out. Three 10-minute showers a week. Meals pushed through a flap in the door. Enforced idleness in a concrete box, year after year.

According to corrections reports, Manuel became a cutter at 17 — slicing his arms with tiny fragments of glass and metal and watching the blood flow.

"It gave me relief from the intolerable numbness," he said.

At different times over the years he went on a hunger strike, overdosed on pills and even set himself on fire with a smuggled match and newspaper he tied to his legs with strips of bedsheet. The result wasn't therapy, it was harsher solitary: No clothes, no mattress, no sheet. A bare cell with 24-hour lights, 60-degree temperatures and no view out.

"It's a miracle I haven't totally lost my mind," he said.

In 2007, he testified by video from solitary confinement at a hearing before Jacksonville federal judge Henry Adams. Manuel described a life of "complete hopelessness." When he finished talking about trying to kill himself "to end the pain," Adams called a recess because Manuel's circumstances so upset him he had to leave the courtroom.

University of California psychologist Craig Haney evaluated solitary confinement at three prisons where Manuel has been held, as part of a case filed by a group of inmates. "Glaringly inhumane," wrote Haney in his report, citing "harsh treatment, deprived conditions and excessive punitiveness."

"Ian learned to live under extraordinary control and deprivation," Haney said recently. "He can't undo the effects of almost 20 years on his own. He's facing enormous psychological challenges if he's released."

• • •

The question at the heart of the two Supreme Court cases about to be decided (Sullivan vs. Florida and Graham vs. Florida) is whether it is "cruel and unusual punishment" to sentence children to life in prison without parole when no one was killed.

Joe Sullivan got life without parole for a rape he committed when he was 13. Terrance Graham was 17 when he got the same sentence for violating probation after an armed robbery. Attorney Bryan Stevenson, who is also Manuel's lawyer, argued in the Sullivan case:

"The essential feature … of a life without parole sentence is that it imposes a terminal, unchangeable, once-and-for-all judgment upon the whole life of a human being. … Such a judgment cannot rationally be passed on children below a certain age."

The two cases are before the high court because of a ruling in a 2005 case (Roper vs. Simmons) which made it "cruel and unusual punishment" to execute anyone under 18. The defense hopes that the same reasoning applied in that case about execution will also apply in the two cases before the court.

From the 2005 Roper opinion: ". . . it would be misguided to equate the failings of a minor with those of an adult, for a greater possibility exists that a minor's character deficiencies will be reformed."

But reform was never an option for Ian Manuel. Lifers in Florida can't participate in rehabilitative programs. And, the rules are even stricter for lifers in solitary like Manuel, who rarely leave their cells.

"Ian never had a chance," said his victim, Debbie Baigrie.

In 1990, Baigrie, 28, was walking in downtown Tampa when Manuel asked her to change a $20 bill. When she said she had no change, he yelled at her to "give it up" and shot her in the face. When police picked him up for stealing weeks later, he told about the shooting. He was offered a plea deal of 15 years and took it. But the judge sentenced him to life without parole.

"We were shocked, but there was nothing we could do because it was within the sentencing range," said former assistant Hillsborough Public Defender Brian Gonzalez.

When Baigrie recovered, with a scar on her cheek the circumference of a pencil, she tried to help Manuel get a high school equivalency degree. But the Department of Corrections wouldn't allow it. She then wrote him for years and encouraged him not to give up hope.

"What does it say when the victim does more to rehabilitate an inmate than the system?" she asked.

With the high court decision imminent, the Florida Department of Corrections is rushing to do what it didn't attempt for 19 years: rehabilitate Ian Manuel.

"We want to help Ian reintegrate and eventually become a productive member of society," said warden Randy Tifft, who runs Santa Rosa Correctional Institution, where Manuel is.

To this end, Manuel is about to be moved to a more lenient form of solitary, which means he can watch TV in a day room a few hours a week, go to group counseling one hour a week and have canteen snack privileges.

"I'll probably overeat and vomit," he says. "I've been deprived of choices so long I hope I don't trip up."

He's hoping to graduate to the general population in about three months and be an orderly. If he does well, he'll be moved to a prison with more programs for inmates.

"I need to learn to be around other inmates and feel useful. I need to feel connected to other human beings."

The few times in solitary when he felt connected are seared in his mind: About 15 years ago, he went to an appellate hearing in his own case. His father, whom he hadn't seen in years, came.

"My father waved at me," he says.

In 2000, John Pizer, an advocate for prisoners in Arizona, began writing him. The correspondence continued.

"John has been a dear, loyal friend," he says.

A few years ago, a friend of his mother's sent him $50. Around the same time, he went to South Florida to testify as a witness to a prison murder. The prison van stopped along the way for supplies.

"Have you ever had cold water in a bottle?" he asks. "It's the most delicious thing there is."

Once he played basketball. Another time he had an ice cream bar. And, for a short time, he landed in a cell that had a tiny window to the outside.

"On winter afternoons, I would press my face to the glass and feel the warmth from the sun."

He started getting letters from caring people a few years ago and, recently, permission to make a collect call once a week. But what mattered most to him happened last year. He was talking about his case with a social worker from his legal team when it hit him that she really cared about him and his future.

"I cried and cried, right there in front of her," he said. "When it was over, I felt so vulnerable — like I was human."

• • •

His family — mother, father and brother — are dead. His mother's friend says he can live with her. But she and Manuel agree he'll first need several years in an intense residential program.

He plans to go to a six-month program in Montgomery, Ala., run by the Equal Justice Initiative, where his law team works. Then, he'll apply to the Delancey Street Foundation in San Francisco. If he's accepted, he'll go for two to four years.

"Ian has been so traumatized he needs a new reality with residential care and a lot of attention," said Stevenson, his attorney. "We'll do everything we can to get him that if he gets out."

Ian Manuel: "If I get out, I want to do whatever it takes to keep me out."

Delancey Street Foundation prides itself on taking the most difficult people from prison and working with them without charge in a family setting, one on one. The $30 million foundation is self-supporting with residents working for a salary in one of its restaurants, bookstores, coffee shops and furniture moving companies. Delancey Street literature says 70 percent of its residents do not reoffend. Some get college degrees while in the program.

Manuel hopes to graduate from college and eventually work with troubled kids.